Enantioselective separation and zebrafish embryo toxicity of insecticide beta-cypermethrin.
Enantioselective separation and zebrafish embryo toxicity of insecticide beta-cypermethrin.
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DOI：
10.1016/s1001-0742(09)60171-6
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发表时间：
2010
影响因子：
6.9
通讯作者：
Chao Xu;W. Tu;C. Lou;Yingying Hong;Mei-rong Zhao
中科院分区：
文献类型：
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作者：
Chao Xu;W. Tu;C. Lou;Yingying Hong;Mei-rong Zhao
由于对映体在毒理学和环境命运上的差异，手性污染物的对映体选择性受到越来越多的关注。在本研究中，杀虫剂高效氯氰菊酯(β-CP)的对映体在选定的手性柱上进行了分离，并用斑马鱼胚胎-幼体试验评价了对映体的毒性。β-CP对映体在Chiralcel OD和Chiralpak AD柱上基线分离，用圆二色谱(CD)检测，检测波长为236 nm。在较低温度(例如，20°C)和较低水平的极性修饰剂下，可以实现更好的分离。在Chiralcel OD上得到了纯的对映体。记录了对映体的圆二色谱。通过将洗脱顺序与以前的类似研究进行比较，确定了β-CP对映体的绝对构型。将不同对映体用于斑马鱼胚胎试验，结果表明，β-CP对映体选择性地诱导卵黄囊肿胀、心包肿胀和畸形体。1R-顺-αS和1R-反式αS对映体在浓度为0.1 mg/L时表现出较强的发育毒性，而1S-顺-αR和1S-反式αR在较高浓度(如0.3 mg/L)时无致畸作用。结果表明，在评价β-CP的生态毒理效应时，应考虑其对映体选择性毒理作用。
Enantioselectivity of chiral pollutants is receiving growing concern due to the difference in toxicology and environment fate between enantiomers. In this study, enantiomers of insecticide beta-cypermethrin (beta-CP) were separated on selected chiral column by HPLC, and the toxicity of enantiomers was evaluated using the zebrafish embryo-larval assays. The enantiomers of beta-CP were baseline separated on Chiralcel OD and Chiralpak AD columns and detected by circular dichroism (CD) at 236 nm. Better separation could be achieved at lower temperature (e.g., 20°C) and with lower levels of polar modifiers. Pure enantiomers were obtained on Chiralcel OD. The CD spectra of enantiomers were recorded. By comparing the elution order with a previous similar study, the absolute configuration of beta-CP enantiomers was determined. The individual enantiomers were used in zebrafish embryo test, and the results showed that beta-CP enantioselectively induced yolk sac edema, pericardial edema and crooked body. The 1R-cis-αS and 1R-trans-αS enantiomers showed strong developmental toxicities at concentration of 0.1 mg/L, while the 1S-cis-αR and 1S-trans-αR induced no malformations at higher concentration (e.g., 0.3 mg/L). The results suggest that the enantioselective toxicological effects of beta-CP should be considered when evaluating its ecotoxicological effects.